EP0576868A1 - Medical articles - Google Patents
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- Publication number
- EP0576868A1 EP0576868A1 EP93109084A EP93109084A EP0576868A1 EP 0576868 A1 EP0576868 A1 EP 0576868A1 EP 93109084 A EP93109084 A EP 93109084A EP 93109084 A EP93109084 A EP 93109084A EP 0576868 A1 EP0576868 A1 EP 0576868A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acetylsalicylic acid
- medical
- esterified
- equipment according
- esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002148 esters Chemical class 0.000 claims abstract description 19
- 229920000642 polymer Polymers 0.000 claims abstract description 15
- 239000000654 additive Substances 0.000 claims abstract description 8
- 239000008280 blood Substances 0.000 claims abstract description 8
- 210000004369 blood Anatomy 0.000 claims abstract description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 6
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical class CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 30
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 25
- 239000004014 plasticizer Substances 0.000 claims description 8
- -1 acetylsalicylic acid ester Chemical class 0.000 claims description 7
- 150000002191 fatty alcohols Chemical class 0.000 claims description 4
- 238000007493 shaping process Methods 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 abstract description 3
- 238000005886 esterification reaction Methods 0.000 abstract description 3
- 238000000465 moulding Methods 0.000 abstract 2
- TVYRJQXMQNZLNO-UHFFFAOYSA-N 3-acetyl-2-hydroxybenzoic acid Chemical compound CC(=O)C1=CC=CC(C(O)=O)=C1O TVYRJQXMQNZLNO-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 238000000576 coating method Methods 0.000 description 8
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 229960002897 heparin Drugs 0.000 description 7
- 229920000669 heparin Polymers 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 239000011265 semifinished product Substances 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- KGLVYIGKGJTMAF-UHFFFAOYSA-N 2,3-bis[(2-acetyloxybenzoyl)oxy]propyl 2-acetyloxybenzoate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OCC(OC(=O)C=1C(=CC=CC=1)OC(C)=O)COC(=O)C1=CC=CC=C1OC(C)=O KGLVYIGKGJTMAF-UHFFFAOYSA-N 0.000 description 1
- 0 CC(CCCC1)C1C(*CC(*)NC1*C1)=O Chemical compound CC(CCCC1)C1C(*CC(*)NC1*C1)=O 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N CC1CCCCC1 Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008207 working material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/0005—Use of materials characterised by their function or physical properties
- A61L33/0052—Plasticizers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
- A61L29/16—Biologically active materials, e.g. therapeutic substances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/0005—Use of materials characterised by their function or physical properties
- A61L33/0011—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
- A61L33/0041—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate characterised by the choice of an antithrombatic agent other than heparin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/105—Esters; Ether-esters of monocarboxylic acids with phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/42—Anti-thrombotic agents, anticoagulants, anti-platelet agents
Definitions
- the invention relates to medical tools such as catheters, tubes, containers, molded parts and the like made of polymeric materials, these tools having special equipment for increasing blood compatibility when in contact with blood or blood-like liquids.
- a coated catheter is known, which is based on a tube made of rubber or an elastomer.
- This catheter tube is coated on the outer and / or inner wall with a hydrophilic polyacrylate or methacrylate, in particular with a hydroxyalkyl or a hydroxyalkoxy alkyl acrylate or methacrylate, each with lower alkyl residues.
- the invention is based on the consideration of adding acetylsalicylic acid esters or mixed esters as additives to the starting polymer, which approximate the quotient 1.0 in terms of blood compatibility with its relative coagulation parameter.
- acetylsalicylic acid esters or mixed esters as additives to the starting polymer, which approximate the quotient 1.0 in terms of blood compatibility with its relative coagulation parameter.
- plasticized polyvinyl chloride as the starting material for the production of medical equipment, it has proven to be advantageous that the PVC formulations based on zinc and calcium which are customary today for such applications are supplemented according to the invention by the acetylsalicylic acid esters or mixed esters mentioned.
- a dosage rate of 0.01 to 2.0 percent by weight has proven to be expedient.
- esters or mixed esters according to the formula can be mixed in a proportion of between 0.01 and 25 percent by weight of the starting polymer, with the addition of the percentages by weight of the acetylsalicylic acid mixed ester taking place in each case to 100 percent by weight of the starting polymer.
- acetylsalicylic acid with saturated and / or unsaturated fatty alcohols C2 to C24 according to the formula is esterified.
- R is synonymous with the saturated and / or unsaturated fatty alcohols C2 to C24.
- the acetylsalicylic acid with a glycerin according to the formula be esterified.
- acetylsalicylic acid according to the invention with glycol according to the formula can be esterified and finally the esterification of acetylsalicylic acid with neopentyl alcohol according to the formula respectively.
- acetylsalicylic acid can be added via amide groups to substances containing amino groups according to the following formula be bound. This improves the sliding properties of polymer melts mixed with this compound.
- these acetysalicylic acid esters or mixed esters or partial esters can represent the chain termination of a polymer plasticizer.
- the usual plasticizers can already be equipped according to the invention. which are then mixed into the starting polymer in the amount customary in the formulation.
- a polymer plasticizer based on adipic acid and 1,3-butanediol is terminated with acetylsalicylic acid as an example:
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Surgery (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Materials For Medical Uses (AREA)
Abstract
Description
Die Erfindung betrifft medizinische Arbeitsmittel wie Katheter, Schläuche, Behälter, Formteile und dergleichen aus polymeren Materialien, wobei diese Arbeitsmittel eine besondere Ausstattung zur Erhöhung der Blutkompatibilität bei der Berührung mit Blut oder blutähnlichen Flüssigkeiten aufweisen.The invention relates to medical tools such as catheters, tubes, containers, molded parts and the like made of polymeric materials, these tools having special equipment for increasing blood compatibility when in contact with blood or blood-like liquids.
Aus der DE-A 19 30 136 ist ein beschichteter Katheter bekannt, welcher als Basis aus einem Schlauch aus Gummi oder einem Elastomeren besteht. Dieser Katheterschlauch ist an der Außen- und/oder Innenwand mit einem hydrophilen Polyacrylat bzw. -Methacrylat, insbesondere mit einem Hydroxialkyl- oder einem Hydroxialkoxi-Alkyl-Acrylat bzw. -Methacrylat mit jeweils niederen Akylresten beschichtet.From DE-A 19 30 136 a coated catheter is known, which is based on a tube made of rubber or an elastomer. This catheter tube is coated on the outer and / or inner wall with a hydrophilic polyacrylate or methacrylate, in particular with a hydroxyalkyl or a hydroxyalkoxy alkyl acrylate or methacrylate, each with lower alkyl residues.
Weiterhin ist es bekannt, derartige medizinische Arbeitsmittel mit einer Beschichtung aus Heparin zu versehen. Diese Heparin-Beschichtungsverfahren arbeiten über APTES- und TDMAC-Brücken. Mit dieser Heparin-Beschichtung wird das Anhaften von Blutplättchen an der Oberfläche des medizinischen Arbeitsmittels verhindert und gleichzeitig die intrinsische Koagulation desaktiviert. Ausführungen zum Beschichtungsverfahren mit Heparin über TDMAC-Brücken finden sich bei G.A. Grode, R.D. Falb, J.P. Crowley in J. Biomed. Mater. Res. Symp., 3, 77 (1972). Entsprechende Hinweise zur Beschichtung mit Heparin über APTES-Brücken finden sich bei R.L. Merker, L.J. Elyasch, S.W. Mayhew, J.Y.C. Wang in Proc. Artif. Heart Conf., 1969, Seite 29.It is also known to provide such medical work tools with a coating made of heparin. These heparin coating processes work via APTES and TDMAC bridges. This heparin coating prevents platelets from adhering to the surface of the medical device and at the same time deactivates intrinsic coagulation. Information on the coating process with heparin via TDMAC bridges can be found at G.A. Grode, R.D. Falb, J.P. Crowley in J. Biomed. Mater. Res. Symp., 3, 77 (1972). Corresponding information on coating with heparin via APTES bridges can be found at R.L. Merker, L.J. Elyasch, S.W. Mayhew, J.Y.C. Wang in Proc. Artif. Heart Conf., 1969, page 29.
Alle diese Verfahren haben den prinzipiellen Nachteil, daß sie technisch aufwendig und sehr arbeitsintensiv sind. So läuft eine Heparinisierung bei beiden genannten Verfahren in mehreren zusätzlichen Arbeits- und Beschichtungszyklen ab.All of these processes have the fundamental disadvantage that they are technically complex and very labor intensive. In both of the methods mentioned, heparinization takes place in several additional working and coating cycles.
Ein weiterer wesentlicher Nachteil dieser bekannten Verfahren ist, daß die auf diese Weise hergestellten medizinischen Halbzeuge sterilisiert werden müssen, weil die Beschichtung mit Heparin mikrobiell abgebaut werden kann. Da nach der Konfektion der Halbzeuge zu Fertigprodukten eine Gesamtsterilisation erforderlich ist, ist hier als weiterer Nachteil das erhebliche Risiko einer Mehrfachsterilisation zu nennen.Another major disadvantage of these known methods is that the medical semi-finished products produced in this way have to be sterilized because the coating with heparin can be degraded microbially. Since total sterilization is required after the semi-finished products have been assembled, another disadvantage is the considerable risk of multiple sterilization.
Hier setzt die Erfindung ein, die es sich zur Aufgabe gestellt hat, die zum Stand der Technik genannten Nachteile zu vermeiden und eine Methode zur Erzielung der optimalen Blutkompatibilität bei medizinischen Halbzeugen und Fertigprodukten aufzuzeigen, bei der über das medizinische Arbeitsmittel weder das biologische System negativen Auswirkungen ausgesetzt ist noch das Material, aus dem das medizinische Arbeitsmittel gefertigt ist durch Einwirkung des biologischen Systems so weit geschädigt werden kann, daß es die vorgesehene Funktion nicht mehr erfüllt. Erfindungsgemäß wird dazu vorgeschlagen, daß in das Ausgangspolymere vor der eigentlichen Formgebung eine definierte Menge von Acetylsalicylsäureestern bzw -mischestern als Zuschlagstoffe eingemischt sind.This is where the invention comes in, which has set itself the task of avoiding the disadvantages mentioned in the prior art and of demonstrating a method for achieving the optimal blood compatibility in the case of semi-finished medical products and finished products, in which neither the biological system has negative effects via the medical equipment the material from which the medical working material is made is still exposed to the effects of the biological system to such an extent that it no longer fulfills the intended function. According to the invention, it is proposed that a defined amount of acetylsalicylic acid esters or esters be mixed as additives into the starting polymer before the actual shaping.
Die Erfindung geht von der Überlegung aus, dem Ausgangspolymeren alsAdditive Acetylsalicylsäureester bzw. -mischester zuzusetzen, die den Werkstoff von der Blutkompatibilität her mit seinem relativen Gerinnungsparameter dem Quotienten 1,0 annähern. So hat es sich bei der Verwendung von weichmacherhaltigem polyvinylchlorid als Ausgangsmaterial für die Herstellung medizinischer Arbeitsmittel als vorteilhaft herausgestellt, daß die heute für solche Anwendungszwecke üblichen PVC-Rezepturen auf Basis Zink und Kalzium erfindungsgemäß durch die genannten Acetylsalicylsäureester bzw. - mischester ergänzt werden. Hierbei hat sich als zweckmäßig eine Dosierungsrate von 0,01 bis 2,0 Gewichtsprozent erwiesen.The invention is based on the consideration of adding acetylsalicylic acid esters or mixed esters as additives to the starting polymer, which approximate the quotient 1.0 in terms of blood compatibility with its relative coagulation parameter. Thus, when using plasticized polyvinyl chloride as the starting material for the production of medical equipment, it has proven to be advantageous that the PVC formulations based on zinc and calcium which are customary today for such applications are supplemented according to the invention by the acetylsalicylic acid esters or mixed esters mentioned. A dosage rate of 0.01 to 2.0 percent by weight has proven to be expedient.
Bei Verwendung von reiner Acetylsalicylsäure der Formel
hat sich herausgestellt, daß eine Dosierungsrate von 2 Gewichtsprozent 100 Gewichtsprozent des Ausgangspolymeren als optimale Dosierungsrate zugemischt werden.When using pure acetylsalicylic acid of the formula
it has been found that a dosage rate of 2 percent by weight and 100 percent by weight of the starting polymer are admixed as the optimal dosage rate.
In bestimmten Fällen kann es zweckmäßig sein, anstatt der reinen Acetylsalicylsäure, Acetylsalicylsäureester oder Acetylsalicylsäure-Mischester als Zuschlagsstoff einzusetzen. Derartige Ester bzw. Mischester nach der Formel
können in einem Mengenanteil zwischen 0,01 und 25 Gewichtsprozent dem Ausgangspolymeren beigemischt werden, wobei die Zumischung der Gewichtsprozentanteile des Acetylsalicylsäure-Mischesters jeweils zu 100 Gewichtsprozent des Ausgangspolymeren erfolgt.In certain cases it may be appropriate to use as an additive instead of the pure acetylsalicylic acid, acetylsalicylic acid ester or mixed acetylsalicylic acid ester. Such esters or mixed esters according to the formula
can be mixed in a proportion of between 0.01 and 25 percent by weight of the starting polymer, with the addition of the percentages by weight of the acetylsalicylic acid mixed ester taking place in each case to 100 percent by weight of the starting polymer.
Es hat sich als zweckmäßig erwiesen, daß die Acetylsalicylsäure mit gesättigten und/oder ungesättigten Fettalkoholen C₂ bis C₂₄ gemäß der Formel
verestert ist. Bei dieser Formel ist R das Synonym für die gesättigten und/oder ungesättigten Fettalkohole C₂ bis C₂₄.It has proven to be useful that the acetylsalicylic acid with saturated and / or unsaturated fatty alcohols C₂ to C₂₄ according to the formula
is esterified. In this formula, R is synonymous with the saturated and / or unsaturated fatty alcohols C₂ to C₂₄.
Gemäß einem Heiteren Ausführungsbeispiel kann die Acetylsalicylsäure mit einem Glyzerin gemäß der Formel
verestert sein.According to a cheerful embodiment, the acetylsalicylic acid with a glycerin according to the formula
be esterified.
Eine weitere Möglichkeit besteht erfindungsgemäß darin, die Acetylsalicylsäure mit Polyethylenglykol gemäß der Formel
n = 3 - 25 000
zu verestern, wobei n = 3 bis 25000 ist.Another possibility according to the invention consists in the acetylsalicylic acid with polyethylene glycol according to the formula
n = 3 - 25,000
to esterify, where n = 3 to 25,000.
Weitere Veresterunsmöglichkeiten bestehen darin, daß die Acetylsalicylsäure mit Pentaerythit gemäß der nachfolgenden Formel
verestert ist.Further esterification possibilities are that the acetylsalicylic acid with pentaerythite according to the following formula
is esterified.
Des weiteren kann die Acetylsalicylsäure erfindungsgemäß mit Glykol gemäß der Formel
verestert sein und schließlich kann die Veresterung der Acetylsalicylsäure mit Neopentylalkohol gemäß der Formel
erfolgen.Furthermore, the acetylsalicylic acid according to the invention with glycol according to the formula
can be esterified and finally the esterification of acetylsalicylic acid with neopentyl alcohol according to the formula
respectively.
Weiter kann die Acetylsalicylsäure über Amidgruppen an aminogruppenhaltige Substanzen entsprechend der nachfolgenden Formel
gebunden werden. Damit werden die Gleiteigenschaften von mit dieser Verbindung versetzten Polymerschmelzen verbessert.Furthermore, acetylsalicylic acid can be added via amide groups to substances containing amino groups according to the following formula
be bound. This improves the sliding properties of polymer melts mixed with this compound.
Die vorgenannten Beispiele zeigen die erfindungsgemäße Möglichkeit, daß Ausgangspolymere vor der eigentlichen Formgebung mit Acetylsalicylsäureestern bzw. -mischestern als Zuschlagstoffe auszustatten. Diese Zuschlagstoffe können andere Zuschlagsmaterialien entsprechend ergänzen. Das wesentliche Merkmal dieser erfindungsgemäßen Zuschlagstoffe wird jedoch darin gesehen, daß die damit ausgestatteten medizinischen Arbeitsmittel die Blutplättchen-Aggregation verhindern und die intrinsische Koagulation desaktivieren. Eine Vorsterilisierung der Halbzeuge ist nicht mehr erforderlich, da deren erfindungsgemäße Ausstattung entgegen der bisher üblichen Heparin-Beschichtung nicht mehr mikrobiell abgebaut werden kann.The abovementioned examples show the possibility according to the invention that starting polymers are provided with acetylsalicylic acid esters or mixed esters as additives before the actual shaping. These aggregates can complement other aggregate materials accordingly. The essential feature of these additives according to the invention, however, is seen in the fact that the medical tools equipped with them prevent platelet aggregation and deactivate the intrinsic coagulation. Pre-sterilization of the semi-finished products is no longer necessary, since their equipment according to the invention can no longer be degraded microbially, in contrast to the heparin coating previously used.
Neben der direkten Zumischung der Acetylsalicylsäureester bzw. -mischester zu dem Ausgangspolymeren können diese Acetysalicylsäureester bzw. -mischester bzw. -teilester den Kettenabschluß eines Polymerweichmachers darstellen. Auf diese weise lassen sich die üblichen Weichmacher bereits erfindunasgemäß ausstatten. die dann in der rezepturüblichen Menge dem Ausgangspolymeren beigemischt werden.In addition to the direct admixture of the acetylsalicylic acid esters or mixed esters to the starting polymer, these acetysalicylic acid esters or mixed esters or partial esters can represent the chain termination of a polymer plasticizer. In this way, the usual plasticizers can already be equipped according to the invention. which are then mixed into the starting polymer in the amount customary in the formulation.
In der nachstehenden Formel ist als Beispiel ein Polymerweichmacher basierend auf Adipinsäure und 1,3 Butandiol endstandig mit Acetylsalicylsäure terminiert:
Die nachfolgenden Beispiele zeigen die Verwendungsmöglichkeit der erfindungsgemäßen Acetylsalicylsäureester bzw. -mischester bzw. -teilester als Zuschlagstoffe für polymere Materialien zur Herstellung medizinischer Arbeitsmittel.The following examples show the possibility of using the acetylsalicylic acid esters or mixed esters or partial esters according to the invention as additives for polymeric materials for the production of medical equipment.
-
1.1 100 Teile S-PVC
10-90 Teile Weichmacher
1-10 Teile epoxidierte Öle
0,1-1 Teile Metallseifen
0,1-1,5 Teile Gleitmittel
0,2-2 Teile Glycerin tri (Acetylsalicylat)1.1 100 parts S-PVC
10-90 parts plasticizer
1-10 parts of epoxidized oils
0.1-1 parts of metal soaps
0.1-1.5 parts of lubricant
0.2-2 parts of glycerol tri (acetyl salicylate) -
1.2 100 Teile S-PVC
10-90 Teile Polyglycoladipat, Acetylsalicylsäure-terminiert
1-10 Teile epoxidierte Öle
0-90 Teile Weichmacher
0,1-1 Teile Metallseifen
0,1-1,5 Teile Gleitmittel1.2 100 parts S-PVC
10-90 parts polyglycol adipate, acetylsalicylic acid terminated
1-10 parts of epoxidized oils
0-90 parts plasticizer
0.1-1 parts of metal soaps
0.1-1.5 parts of lubricant
100 Teile Polyurethan
0,5-20 Teile Polyglycoladipat, Acetylsalicylsäure-terminiert100 parts of polyurethane
0.5-20 parts polyglycol adipate, acetylsalicylic acid terminated
100 Teile Polyethylen
0,01-5 Teile N-Stearoyl-N'Acetylsalicylsäureethylendiamin100 parts of polyethylene
0.01-5 parts of N-stearoyl-N'acetylsalicylic acid ethylenediamine
100 Teile Polypropylen
0,01-5 Teile Ester von Acetylsalicylsäure und C 12 bis C 24 Fettalkoholen100 parts of polypropylene
0.01-5 parts of esters of acetylsalicylic acid and C 12 to C 24 fatty alcohols
10 - 90 Teile Polymerweichmacher, Acetylsalicylsäure-terminiert
0 - 90 Teile Weichmacher10 - 90 parts polymer plasticizer, acetylsalicylic acid terminated
0 - 90 parts plasticizer
Claims (10)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4221665 | 1992-07-02 | ||
| DE4221665A DE4221665C1 (en) | 1992-07-02 | 1992-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0576868A1 true EP0576868A1 (en) | 1994-01-05 |
| EP0576868B1 EP0576868B1 (en) | 2000-04-05 |
Family
ID=6462283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP93109084A Expired - Lifetime EP0576868B1 (en) | 1992-07-02 | 1993-06-05 | Medical articles |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0576868B1 (en) |
| JP (1) | JPH06169983A (en) |
| AT (1) | ATE191350T1 (en) |
| DE (1) | DE4221665C1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4341628A1 (en) * | 1993-12-07 | 1995-07-06 | Rehau Ag & Co | Process for the production of medical work equipment |
| CN105017515A (en) * | 2015-07-20 | 2015-11-04 | 湖南华腾制药有限公司 | Preparation method of polyethylene glycol-modified material |
| CN105017519A (en) * | 2015-07-20 | 2015-11-04 | 湖南华腾制药有限公司 | Preparation method of polyethylene glycol-modified micromolecule drug |
| CN110668947A (en) * | 2019-10-14 | 2020-01-10 | 新乡海盈生物科技有限责任公司 | O-hydroxybenzoic acid polyglycol ester compound and synthesis preparation method and medical application thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19638570A1 (en) * | 1996-09-20 | 1998-03-26 | Bayer Ag | Active ingredient-containing thermoplastic polyurethanes |
| EP1485141B1 (en) | 2002-03-20 | 2008-08-06 | Gambro Lundia AB | Extracorporeal circuit with tube for medical applications |
| DE102011076833A1 (en) * | 2011-05-31 | 2012-12-06 | Atmos Medizintechnik Gmbh & Co. Kg | Wound drainage procedures |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1013235A (en) * | 1963-01-17 | 1965-12-15 | Yoshitomi Pharmaceutical | Method of preparing polyhydric alcohol esters of acetylsalicylic acid |
| DE2812174A1 (en) * | 1977-03-22 | 1978-09-28 | Snam Progetti | BIOLOGICALLY COMPATIBLE OBJECTS |
| EP0136916A2 (en) * | 1983-10-03 | 1985-04-10 | Sumitomo Electric Industries Limited | Anthithrombic resin composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5082925A (en) * | 1990-08-16 | 1992-01-21 | Ethicon, Inc. | Homopolymers and copolymers of salicylate lactones |
-
1992
- 1992-07-02 DE DE4221665A patent/DE4221665C1/de not_active Expired - Fee Related
-
1993
- 1993-06-05 AT AT93109084T patent/ATE191350T1/en not_active IP Right Cessation
- 1993-06-05 EP EP93109084A patent/EP0576868B1/en not_active Expired - Lifetime
- 1993-07-01 JP JP5163483A patent/JPH06169983A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1013235A (en) * | 1963-01-17 | 1965-12-15 | Yoshitomi Pharmaceutical | Method of preparing polyhydric alcohol esters of acetylsalicylic acid |
| DE2812174A1 (en) * | 1977-03-22 | 1978-09-28 | Snam Progetti | BIOLOGICALLY COMPATIBLE OBJECTS |
| EP0136916A2 (en) * | 1983-10-03 | 1985-04-10 | Sumitomo Electric Industries Limited | Anthithrombic resin composition |
Non-Patent Citations (1)
| Title |
|---|
| DERWENT JAPANESE PATENTS REPORT Week 6800, Derwent Publications Ltd., London, GB; AN 66-30851 & JP-B-43 003 291 (YOSHITOMI) * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4341628A1 (en) * | 1993-12-07 | 1995-07-06 | Rehau Ag & Co | Process for the production of medical work equipment |
| CN105017515A (en) * | 2015-07-20 | 2015-11-04 | 湖南华腾制药有限公司 | Preparation method of polyethylene glycol-modified material |
| CN105017519A (en) * | 2015-07-20 | 2015-11-04 | 湖南华腾制药有限公司 | Preparation method of polyethylene glycol-modified micromolecule drug |
| CN110668947A (en) * | 2019-10-14 | 2020-01-10 | 新乡海盈生物科技有限责任公司 | O-hydroxybenzoic acid polyglycol ester compound and synthesis preparation method and medical application thereof |
| WO2021073038A1 (en) * | 2019-10-14 | 2021-04-22 | 新乡海盈生物科技有限责任公司 | O-hydroxybenzoic acid polyglycol ester compound, and synthetic preparation method and pharmaceutical use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE191350T1 (en) | 2000-04-15 |
| DE4221665C1 (en) | 1993-08-12 |
| EP0576868B1 (en) | 2000-04-05 |
| JPH06169983A (en) | 1994-06-21 |
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